Does saying this imply that we both are schlechte Spieler, but that that guy is even worse? That is, if I use the comparative of an adjective, do the objects posses the quality that the adjective describe?

A last example. Is saying

Lola ist schöner als ihre Schwester.

the same as the following?

Die Schwester Lolas ist hässlicher als sie.

In the picture below, I try to express this idea. There, the speaker has a (oversimplified) criterion to decide what is schön, what is hässlich. Are those sentences equally appropriated for both lines?

Remark: I don't think the question might make sense for everybody. There are languages, however, presenting this feature. You say "is more beautiful than..." and it implies that both objects you compare are sometimes considered beautiful, not only that you consider one of them more beautiful than the other. In some sociological contexts it is so in Spanish, for instance. If you say there Mi amiga es más inteligente que tú, that means that both mi amiga and tú are considered intelligent.

Edit 1: Thanks to the comments of Em1, now I know that the tag "sociolinguistics" in this question, wasn't enough to express the true spirit of my question. It's not about the logical aspects in comparing objects (logic is not the only aspect involved in languages), but about how is sometimes this comparison perceived.

Edit 2: Again due to the comments of Em1, I have to clear things up. I never have spoken about a lack of possibility to compare things neutrally. The core part of the post, although it wasn't inlcuded in the first version, are the last questions. (Spanish is my mother tongue, so I know that when you compare persons, you have to be subtle with the choice of the adjectives). It's aimed to avoid me social problems by using comparation in German. Last, but not least, see the question of Em1 in Spanish.SE — an utterly interesting argument!

If you say A is better than B then this means that A is better than B but does not qualify if A and B are good or bad. A and B can be the world's best players and they are in finals of an competition or they're simply some noobs who play for fun only.
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Em1Aug 23 '13 at 7:57

1

I like this question a lot! I have never thought about that...
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EmanuelAug 23 '13 at 9:55

Note the little "noch" above. With A ist noch XYZer als B, you can make it explicit that both A and B are XYZ (to a high degree). Compare "A is even more XYZ than B."

Lara ist schöner als ihre Schwester.

Here, Lara is beautiful. In isolation, I would interpret this sentence such that her sister is at least somewhat beautiful.

Lolas ist hässlicher als ihre Schwester.

Here, Lolas is ugly. Lara could be ugly or beautiful, or something in between. If you had considered Lolas beautiful, you would not have chosen "ugly,", as it carries pretty strong negative connotations. So these two sentences are not quite the same.

Ich bin intelligenter als du.

Most likely, this means that "I" think "you" are stupid.

Du bist intelligenter als ich.

In general, "I" don't like to admit I'm stupid, so the above could very well mean "You are a genius (but I'm no idiot either.)

However, these sentences rarely occur by themselves without context, which might shift the actual meaning either way.

Observe that in "A is XYZer als B", this often implies that at least A is indeed XYZ. Consider the following dialogue:

You're right. It's a logical problem and not based on language. For that reason OP is wrong when he said that the Spanish language handles this differently as if he were true the Spanish language had a great lack of representing and describing real-life data in words.
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Em1Aug 23 '13 at 12:30

I don't know any Spain, but I would not be surprised if, given the right context, that Spanish phrase could be taken either way as well. A sentence such as "Tom is more intelligent than Peter", without any context I would consider neither Peter nor Tom as stupid. Perhaps it would be helpful to ask then, or think about, how Spanish natives would describe the other cases.
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blutorangeAug 23 '13 at 12:42

»Schlechter« and »besser« alone are used for simple comparison of any range without implicit judgement. They may turn the property to its antonym, but not necessarily. They just describe to which direction something goes but does not say anything about where it starts and where it ends. Use an additional »noch« for those words to implicitely tell the comparison is without turning to its antonym, for example noch schlechter would judge both ones to be »schlecht«.

Other words (for example »großartiger«, »hässlicher« or »furchtbarer«) imply a valuation about good or bad for both ones. Using them for comparing keeps the implicit valuation. A ist furchtbarer als B tells that both are terrible. The use of »noch« for those words is used to describe which difference is bigger if you have two comparisons.

Usually, "A spielt besser Schach als B" (or "B spielt schlechter Schach als A") do not connote that A and B are both good (or both bad). If one wanted to express somthing like that one would use
"A spielt noch besser Schach als B" (or "B spiel noch schlechter Schach als A").

Actually, while reading your examples I felt like there might be such a connotation, but I guess that has psychological rather than linguistic reasons - if you hear only positive words and no negative ones, your mental image tends to build up using positive properties only. However, a sentence like "Die erste Partie gewann B, obwohl er für gewöhnlich schlechter Schach spielt als A" might be found in a newspaper report about the chess world championshiop as well as about lousy hobby players.
On the other hand, there are situations were "A ist besser als B" in fact implies that both A and B are "schlecht": "Ich habe gehört, du warst schwer krank?" - "Ja, aber es geht mir langsam besser/ich bin auf dem Wege der Besserung" This means that he/she is still not feeling good.

I absolutely agree to blutorange's answer just want to put it in some other words.

It's a logical problem and has nothing to do with languages at all. The language is just a way of describing and representing the data.

If you compare two items, you do not qualify them. Not at all. That is, you cannot tell from a comparison whether the items in question are good or bad.

If you compare two items, you compare them based on a vague range. An object A might be good in comparison to B but at the same time being bad in to comparison to C.

To take real-life examples. Let's say you and your friend play chess every day for two years now. You can answer my question Who's better? with one of those three answers:

He's a very challenging opponent but I am better.

I do my best but he's better than I.

I cannot tell, we're equally well.

Independent of your answer, I can't tell if you're good or not. My next question would be Who's better? You or Garry Kasparov?. Independent of your origin and your language, you'll laugh about this question and will state that Garry Kasparov is obviously better.
But I still do not know your chess skills.

So, if you compare two items they do not need to be equally well. They only need to be comparable. You cannot compare if it would be more comfortable to live on Mars or on Venus. You can hardly compare the taste of apples and oranges. Some people might have an opinion on that but others not. And those who have an opinion will think differently of that.

Another example. You and your friend go shopping. Your friend takes a blue and a red shirt and tries them. You consider the blue one as quite cool but the red one is really ugly. When your friend asks you which is more beautiful you can confidently respond that the blue shirt is more beautiful than the red one. But still, you think that the red one is ugly. For that reason you might not answer the actual question and instead say that the red one doesn't suit them and is actually very ugly.

This is the reason why you think that two objects must be on the same page to be comparable. This is why people laugh if you compare two significantly opposing objects.

Lastly, I'm sure that this is not different in the Spanish language. Otherwise, I see a distinctive lack in this language by not being able to address comparisons appropriately.

Perhaps this is common in many cultures/languages, but I don't think I can fully agree on this being a problem of logic only. Many phrases and expressions carry a certain nuance and implied message, I don't quite see why it should be impossible a construction with a comparative can get a certain connotation and not carry the full logical meaning. Consider "We're both equally well." and "We're both equally bad." Logically, they should mean the same, but do they really practically? Or a more extreme case, "We're both equally perfect. Our level of perfectness is 0."
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blutorangeAug 23 '13 at 13:16

I'm not answering my own question, but I'd like to briefly elaborate on some ideas that falkb and user unknown mentioned: both lead to the conclusion that comparing depend on the nature of the adjective.

Absolute character

If you wish to compare, say, the height, you don't fix a criterion. There's a convention called meter, which is absolute:

Arbitrary character

Here the criterion is set by the speaker. He or she determines what is schön, what is hässlich. Strictly speaking, in each case the original phrase

Lola ist schöner als ihre Schwester

is valid. Nevertheless there are better expressions for each case:

a) Lola ist ja schön! (as an answer to the question "Wer ist schöner?", tacitly implying that the sister is not beautiful. Contrasting is always possible; comparation isn't so appropriate.)

I still stumble on "schlecht". The adjective is < 0 on your scales, but its Komparativ can also be used to tell about the comparison of 2 things > 0. Not sure how this fits to the 3 groups above.
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falkbAug 26 '13 at 10:14

@falkb Yeah, it seems I forgot the original adjective :/ So I guess that if you compare "A schlechter als B", or "B besser als A" that doesn't mean both are bad or good: as your answer mentions, in that case one wishes to emphasize, one uses noch schlechter/besser
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c.p.Aug 27 '13 at 5:26

(which implies that the meaning of comparing is adjective-depending -- not desirable feature?)
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c.p.Aug 27 '13 at 5:26

not sure if your latest comment is a question or state. Please, could you put it in other words?
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falkbAug 27 '13 at 6:12

@falkb The first was a statement; the second, a question. I meant that I'm not sure that if comparison being an adjective-dependent feature is a desirable characteristic of the language. (I'll erase that comment to avoid confusion).
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c.p.Aug 27 '13 at 7:32